Reaktion #332632

Reaktionsgleichung

Hydroxylamine hydrochloride

Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-oxoacetate

Intermediate 121

Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-oxoacetate

pyridine

→

ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-[(2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-(hydroxyimino)acetate

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a yellow solution
2. 2
   EinengenThe resulting solution was concentrated to an oil
3. 3
   SonstigeThe residue was purified by chromatography on SiO2 using 5-40% EtOAc/hexane
4. 4
   workup.ADDITIONA total of 11.93 g (87%) of the title product as a mixture of oxime isomers
5. 5
   Sonstigewas obtained as a yellow oil

Vorschrift

Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-oxoacetate (Intermediate 121, 13.4 g, 21.85 mmol) was slurried in isopropanol (150 ml), and pyridine (124 ml, 1529.70 mmol) was added to give a yellow solution. Hydroxylamine hydrochloride (1.670 g, 24.04 mmol) was added, and the suspension was stirred at room temperature for approximately 16 hours. The resulting solution was concentrated to an oil. The residue was purified by chromatography on SiO2 using 5-40% EtOAc/hexane. A total of 11.93 g (87%) of the title product as a mixture of oxime isomers was obtained as a yellow oil.

Quelle